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Engineering an NIR rhodol derivative with spirocyclic ring-opening activation for high-contrast photoacoustic imaging.


ABSTRACT: Molecular probes that enable high-contrast photoacoustic (PA) imaging of cellular processes are valuable tools for in vivo studies. Design of activatable PA probes with high contrast remains elusive. We develop a new NIR rhodol derivative, Rhodol-NIR, with a large extinction coefficient, low quantum yield and structural switching from a 'ring-open' form to a 'closed' spirolactone upon esterification. This structural transition, together with the ideal photophysical properties, enables the development of activatable probes for high-contrast PA imaging via a target-specific de-esterification reaction. This strategy is demonstrated using a PA probe designed for a tumor biomarker, human NAD(P)H: quinone oxidoreductase isozyme 1 (hNQO1), which affords high contrast and excellent sensitivity for PA detection and imaging of hNQO1 in living cells and animals. The strategy can provide a new paradigm for engineering activatable PA probes for high-contrast imaging.

SUBMITTER: Liu F 

PROVIDER: S-EPMC7003941 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Engineering an NIR rhodol derivative with spirocyclic ring-opening activation for high-contrast photoacoustic imaging.

Liu Feng F   Shi Xiao X   Liu Xianjun X   Wang Fenglin F   Yi Hai-Bo HB   Jiang Jian-Hui JH  

Chemical science 20190816 40


Molecular probes that enable high-contrast photoacoustic (PA) imaging of cellular processes are valuable tools for <i>in vivo</i> studies. Design of activatable PA probes with high contrast remains elusive. We develop a new NIR rhodol derivative, Rhodol-NIR, with a large extinction coefficient, low quantum yield and structural switching from a 'ring-open' form to a 'closed' spirolactone upon esterification. This structural transition, together with the ideal photophysical properties, enables the  ...[more]

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